Sailing the Caribbean

Trade winds and island-hopping paradise

The Caribbean is the world's most celebrated sailing ground — a 4,000 km arc of islands stretching from the Bahamas in the north to Trinidad in the south, blessed with reliable trade winds, warm clear water, and a culture that revolves around the sea. For sailors, it's a place where passages are short, anchorages are spectacular, and the next island is always within a day's sail.

The British Virgin Islands remain the single most popular charter base in the world. The Sir Francis Drake Channel — a sheltered passage between Tortola, Virgin Gorda, and their satellite islands — offers beginners a gentle introduction to Caribbean sailing while still delivering postcard scenery. The Grenadines, strung between St. Vincent and Grenada, are a step up: longer passages, wilder anchorages, and far fewer crowds. Antigua's English Harbour is legendary among offshore sailors — Nelson's dockyard, a hurricane hole, and the start line of the ARC Atlantic rally. St. Martin's lagoon is the refit and provisioning capital of the Eastern Caribbean, with French and Dutch cultures side by side.

The best season runs from November through May, when the northeast trade winds are consistent and the hurricanes are gone. June through October is hurricane season — most charter operations either haul out or move south below the hurricane belt (Grenada, Trinidad). If you sail in the shoulder seasons of November or May, you'll find lower prices, emptier anchorages, and often excellent conditions.